Pyrrolidine → Z-2-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-propyl-pentanoic acid ethyl ester

HRID 658930Notes

Reaction equation

HRID 658930 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:33])[C:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[CH:31]=O)([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH3:13].N1CCCC1>CO>[CH2:12]([O:14][C:15](=[O:33])[C:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1/[CH:31]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH3:13]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 59428102HCID 59428102, compound

Product 1

HCID 86632098Z-2-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-propyl-pentanoic acid ethyl esterYield 20.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 6-chlorooxindole (9.3 g, 55.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-propyl-pentanoic acid ethyl ester (14 g, 42.9 mmol) in methanol (100 mL) was added pyrrolidine (3.3 g, 47.2 mmol) dropwise. The mixture was then heated at 80° C. for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was purified by flash column to give the title compound (4.2 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-a1e89d9b08174d6b98d2a765e8ba2a01
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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